4-Bromo-2-fluoroaniline → 7-Benzyloxy4-(4-bromo-2-fluoroanilino)-6-methoxyquinazoline hydrochloride

HRID 1596290Notes

Reaction equation

HRID 1596290 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([Cl:20])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[C:26]([F:31])[CH:25]=1>C(O)(C)C>[ClH:20].[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:28][C:27]3[CH:29]=[CH:30][C:24]([Br:23])=[CH:25][C:26]=3[F:31])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 1230504-Bromo-2-fluoroanilineHCID 220308367-(Benzyloxy)-4-chloro-6-methoxyquinazoline hydrochloride

Product 1

HCID 187534737-Benzyloxy4-(4-bromo-2-fluoroanilino)-6-methoxyquinazoline hydrochlorideYield 78%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 7-benzyloxy-4-chloro-6-methoxyquinazoline hydrochloride (8.35 g, 24.8 mmol), (prepared as described for the starting material in Example 4), and 4-bromo-2 fluoroaniline (5.65 g, 29.7 mmol) in isopropanol (200 ml) was heated at reflux for 4 hours. The resulting precipitated solid was collected by filtration, washed with isopropanol and then ether and dried under vacuum to give 7-benzyloxy4-(4-bromo-2-fluoroanilino)-6-methoxyquinazoline hydrochloride (9.46 g, 78%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customThe resulting precipitated solid
  4. filtrationwas collected by filtration
  5. washwashed with isopropanol
  6. dry with materialether and dried under vacuum

Sources & evidence

ORD record
ord-41263176a2a94251b12f65689eb9049b
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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